13395-85-2|2-(tert-Butyl)-4-chlorophenol| Ambeed

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Quality Control of [ 13395-85-2 ] Purity: 95% SDS Specification

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Product Details of [ 13395-85-2 ]

CAS No. :	13395-85-2
Formula :	C₁₀H₁₃ClO
M.W :	184.66
SMILES Code :	OC1=CC=C(Cl)C=C1C(C)(C)C
MDL No. :	MFCD16657845
InChI Key :	YLSXYZWJAZVUBD-UHFFFAOYSA-N
Pubchem ID :	518765

Safety of [ 13395-85-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 13395-85-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	52.74
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.53
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.34
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.32
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.69
Solubility	0.0378 mg/ml ; 0.000205 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.93
Solubility	0.0217 mg/ml ; 0.000118 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.65
Solubility	0.0414 mg/ml ; 0.000224 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.72 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.24

Application In Synthesis of [ 13395-85-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 13395-85-2 ]
Downstream synthetic route of [ 13395-85-2 ]

[ 13395-85-2 ] Synthesis Path-Upstream 1~4

1
[ 106-48-9 ]
[ 75-65-0 ]
[ 13395-85-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	for 48 h; Inert atmosphere	The ligand precursor 3-ter -butyl-5-chlorosalicylaldehyde has been previously reported, and ^{FontWeight="Bold" FontSize="10"}H NMR assignments are included that match well with those in the literature. The yield represents average isolated yields. The precursor to the salicylaldehyde, 2-tert- butyl-4-chlorophenol, was synthesized according to literature procedure. 4-Chlorophenol (Combi-B locks, 8.00 g, 62.2 mmol) was dissolved in tert-butyl alcohol (Aldrich, 1 1.9 mL, 124 mmol), and 7.50 mL of concentrated H₂S0₄ was added dropwise over 5 minutes, turning the solution from a pale yellow to a light orange. The solution was stirred for 2 days, neutralized with Na₂C0₃ (aq), and then extracted into diethyl ether and dried over Na₂S0₄. The product was concentrated and purified by column chromatography (95:5, hex:EtOAc) resulting in a yellow oil (71percent isolated yield). Using a modified Duff reaction, 2-/ert-butyl-4- chlorophenol was formylated as reported by Jacobsen et al. The product was purified by column chromatography (90: 10, hex:EtOAc) to yield a crystalline yellow solid (24percent isolated yield). NMR spectrum in ppm (CDC1₃, 400 MHz): δ 1 1.72 (s, I H); 9.82 (s, IH); 7.46 (d, J = 2.6 Hz, IH); 7.38 (d, J = 2.6 Hz, IH); 1.41 (s, 12H).
68%	at 20℃; for 48 h;	Step 1 : 2-(teff-Butyl)-4-chlorophenol (P19a) To a mixture of 4-chlorophenol (50 g, 0.39 mol) and M3uOH (57.6 g, 0.78 mol) was added cone. H₂S0₄ (40 mL) and the solution was stirred at rt for 48 h, poured into ice-water and extracted with EA twice. The combined organic layers were washed with water (3x) and brine consecutively, dried over Na₂S0₄, filtered, concentrated and purified by CC (PE/EA = 40/1) to give compound P19a (48.5 g, 68percent) as a colorless solid
54%	at 20℃; for 48 h;	To a mixture of p-chlorophenol (19.0 g, 147.8 mmol) and tert-butanol (21.9 g, 295.6 mmol) was added concentrated sulfuric acid (15 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured into ice water (300 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate 95:5) to give the title compound (14.3 g, yield 54percent) as a brown oil. ¹H NMR (300 MHz, CDCl₃) δ 7.21 (d, J=2.7Hz, 1H), 7.02 (dd, J=8.3, 2.7Hz, 1H), 6.60 (d, J=8.7Hz, 1H), 4.95 (br s, 1H), 1.39 (s, 9H).

References: [1] Patent: WO2016/25675, 2016, A1, . Location in patent: Paragraph 0100.
[2] Journal of the American Chemical Society, 2014, vol. 136, # 45, p. 15897 - 15900.
[3] Journal of the American Chemical Society, 2016, vol. 138, # 22, p. 7107 - 7113.
[4] Patent: WO2013/79223, 2013, A1, . Location in patent: Page/Page column 77.
[5] European Journal of Inorganic Chemistry, 2013, # 14, p. 2538 - 2548.
[6] Patent: EP2202223, 2010, A1, . Location in patent: Page/Page column 58-59.
[7] Journal of the American Chemical Society, 1956, vol. 78, p. 4604,4608.

2
[ 88-18-6 ]
[ 13395-85-2 ]
[ 4237-37-0 ]

References: [1] Journal of Organic Chemistry, 2014, vol. 79, # 2, p. 809 - 813.
[2] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479.
[3] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479.
[4] Dalton Transactions, 2008, # 48, p. 6883 - 6885.

3
[ 88-18-6 ]
[ 13395-85-2 ]

References: [1] Synlett, 2018, vol. 29, # 16, p. 2155 - 2160.

4
[ 88-18-6 ]
[ 13395-85-2 ]
[ 4237-37-0 ]
[ 13395-86-3 ]

References: [1] Journal of Organic Chemistry, 2014, vol. 79, # 2, p. 809 - 813.

[ 13395-85-2 ] Synthesis Path-Downstream 1~35

1
[ 13395-85-2 ]
[ 103-71-9 ]
[ 66634-64-8 ]

References: [1]Industrial and Engineering Chemistry, Analytical Edition,1944,vol. 16,p. 304.

2
[ 106-48-9 ]
[ 75-65-0 ]
[ 13395-85-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sulfuric acid; for 48h;Inert atmosphere;	The ligand precursor 3-ter -butyl-5-chlorosalicylaldehyde has been previously reported, and FontWeight="Bold" FontSize="10" H NMR assignments are included that match well with those in the literature. The yield represents average isolated yields. The precursor to the salicylaldehyde, 2-tert- butyl-4-chlorophenol, was synthesized according to literature procedure. 4-Chlorophenol (Combi-B locks, 8.00 g, 62.2 mmol) was dissolved in tert-butyl alcohol (Aldrich, 1 1.9 mL, 124 mmol), and 7.50 mL of concentrated H2S04 was added dropwise over 5 minutes, turning the solution from a pale yellow to a light orange. The solution was stirred for 2 days, neutralized with Na2C03 (aq), and then extracted into diethyl ether and dried over Na2S04. The product was concentrated and purified by column chromatography (95:5, hex:EtOAc) resulting in a yellow oil (71% isolated yield). Using a modified Duff reaction, 2-/ert-butyl-4- chlorophenol was formylated as reported by Jacobsen et al. The product was purified by column chromatography (90: 10, hex:EtOAc) to yield a crystalline yellow solid (24% isolated yield). NMR spectrum in ppm (CDC13, 400 MHz): delta 1 1.72 (s, I H); 9.82 (s, IH); 7.46 (d, J = 2.6 Hz, IH); 7.38 (d, J = 2.6 Hz, IH); 1.41 (s, 12H).
68%	With sulfuric acid; at 20℃; for 48h;	Step 1 : 2-(teff-Butyl)-4-chlorophenol (P19a) To a mixture of 4-chlorophenol (50 g, 0.39 mol) and M3uOH (57.6 g, 0.78 mol) was added cone. H2S04 (40 mL) and the solution was stirred at rt for 48 h, poured into ice-water and extracted with EA twice. The combined organic layers were washed with water (3x) and brine consecutively, dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 40/1) to give compound P19a (48.5 g, 68%) as a colorless solid
54%	With sulfuric acid; at 20℃; for 48h;	To a mixture of p-chlorophenol (19.0 g, 147.8 mmol) and tert-butanol (21.9 g, 295.6 mmol) was added concentrated sulfuric acid (15 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured into ice water (300 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate 95:5) to give the title compound (14.3 g, yield 54%) as a brown oil. 1H NMR (300 MHz, CDCl3) delta 7.21 (d, J=2.7Hz, 1H), 7.02 (dd, J=8.3, 2.7Hz, 1H), 6.60 (d, J=8.7Hz, 1H), 4.95 (br s, 1H), 1.39 (s, 9H).

References: [1]Patent: WO2016/25675,2016,A1 .Location in patent: Paragraph 0100.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 15897 - 15900.
[3]Journal of the American Chemical Society,2016,vol. 138,p. 7107 - 7113.
[4]Patent: WO2013/79223,2013,A1 .Location in patent: Page/Page column 77.
[5]European Journal of Inorganic Chemistry,2013,p. 2538 - 2548.
[6]Patent: EP2202223,2010,A1 .Location in patent: Page/Page column 58-59.
[7]Journal of the American Chemical Society,1956,vol. 78,p. 4604,4608.

3
[ 100-97-0 ]
[ 13395-85-2 ]
[ 135395-82-3 ]
2-tert-Butyl-6-(8-tert-butyl-6-chloro-4H-benzo[e][1,3]oxazin-3-ylmethyl)-4-chloro-phenol [ No CAS ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 1939 - 1942.

4
[ 50-00-0 ]
[ 13395-85-2 ]
[ 124-40-3 ]
[ 175907-50-3 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 1859 - 1868.

5
[ 13395-85-2 ]
[ 612-14-6 ]
1,2-Bis(3-chloro-2-hydroxy-5-methylbenzyl)benzene [ No CAS ]

References: [1]Organic Preparations and Procedures International,1999,vol. 31,p. 328 - 332.

Yield	Reaction Conditions	Operation in experiment
		Some examples of useful donor phenols are: ... 2-tert-octyl-4-eicosyloxyphenol 2,4-dichloro-6-tert-butylphenol 2-tert-butyl-4-chlorophenol 2-tert-butyl-6-bromophenol ...

7
[ 13395-85-2 ]
C₂₃H₂₄ClNO [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 1859 - 1868.

8
[ 13395-85-2 ]
[ 175907-71-8 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 1859 - 1868.

9
[ 13395-85-2 ]
2-tert-Butyl-4-chlor-6-<(2-dimethylamino-1-naphthyl)methyl>phenol [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 1859 - 1868.

10
[ 28069-69-4 ]
[ 13395-85-2 ]
[ 207723-47-5 ]

References: [1]European Journal of Inorganic Chemistry,1998,p. 621 - 627.

11
[ 5454-83-1 ]
[ 13395-85-2 ]
[ 1135825-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; N,N-dimethyl-formamide;	Example 1 Synthesis of 5-(2-tert-Butyl-4-chlorophenoxy)pentanoic Acid Methyl 5-bromovalerate (1.52 mL, 2.09 g, 10.7 mmol), 2-tert-butyl-4-chloro-phenol (2.4 g, 13 mmol) and potassium carbonate (1.4 g, 10.1 mmol) were suspended in dry DMF (10 mL) and stirred for 2 h at 120 C. To the resulting mixture water was added (80 mL) and extracted with ethyl acetate (320 mL). The organic layers were washed two times with 10% sodium hydroxide (220 mL), water (1*20 mL), dried over sodium sulfate and evaporated in vacuo. To afford 3.46 g (quant) crude la that was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) delta ppm 7.21 (d, J=2.6 Hz, 1H), 7.10 (dd, J=8.6, 2.6 Hz, 1H), 6.75 (d, J=8.6 Hz, 1H), 3.97 (t, J=5.8 Hz, 2H), 2.46 (t, J=6.9 Hz, 2H), 1.84-1.94 (m, 4H), 1.36 (s, 9H).

References: [1]Patent: US2009/88435,2009,A1 .

12
[ 50-00-0 ]
[ 13395-85-2 ]
[ 135395-82-3 ]

References: [1]Dalton Transactions,2008,p. 6883 - 6885.

13
[ 88-18-6 ]
[ 13395-85-2 ]
[ 4237-37-0 ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 809 - 813.
[2]Organic Letters,2016,vol. 18,p. 5476 - 5479.
[3]Organic Letters,2016,vol. 18,p. 5476 - 5479.
[4]Dalton Transactions,2008,p. 6883 - 6885.

14
[ 50-00-0 ]
[ 13395-85-2 ]
[ 4730-54-5 ]
1,4,7-tris(3-tert-butyl-5-chloro-2-hydroxybenzyl)-1,4,7-triazacyclononane [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2013,p. 2538 - 2548.

15
[ 13395-85-2 ]
[ 1442432-07-6 ]

References: [1]Patent: WO2013/79223,2013,A1 .

16
[ 13395-85-2 ]
[ 1442432-08-7 ]

References: [1]Patent: WO2013/79223,2013,A1 .

17
[ 13395-85-2 ]
[ 1442430-92-3 ]

References: [1]Patent: WO2013/79223,2013,A1 .

18
[ 13395-85-2 ]
[ 14035-01-9 ]

References: [1]Patent: WO2013/79223,2013,A1 .

19
[ 13395-85-2 ]
[ 1442430-93-4 ]

References: [1]Patent: WO2013/79223,2013,A1 .

20
[ 13395-85-2 ]
[ 1442430-94-5 ]

References: [1]Patent: WO2013/79223,2013,A1 .

21
[ 358-23-6 ]
[ 13395-85-2 ]
[ 1442430-91-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; In dichloromethane; at 0 - 20℃; for 4h;	Step 1 : 2-(terf-Butyl)-4-chlorophenyl trifluoromethanesulfonate (P75a) To a solution of 2-(terf-butyl)-4-chlorophenol (30 g, 0.163 mol) and pyridine (21 mL, 0.26 mol) in dry DCM (500 mL) was added a solution of Tf20 (33 ml, 0.19 mol) in dry DCM (150 mL) at 0C and the solution was stirred for 4 h at rt, poured into 1 M HCI and extracted with DCM. The organic layer was washed with brine, dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 10/1) to give P75a (39 g, 87%) as a colorless liquid.

References: [1]Patent: WO2013/79223,2013,A1 .Location in patent: Page/Page column 107-107.

22
[ 50-00-0 ]
[ 13395-85-2 ]
[ 61798-24-1 ]
C₃₀H₄₄Cl₂N₂O₂ [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2013,p. 3362 - 3369.

23
[ 88-18-6 ]
[ 13395-85-2 ]
[ 4237-37-0 ]
[ 13395-86-3 ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 809 - 813.

24
[ 13395-85-2 ]
[ 86864-60-0 ]
C₁₈H₃₁ClO₂Si [ No CAS ]